# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2128022'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 F6'
_chemical_formula_sum            'C24 H12 F6'
_chemical_formula_weight         414.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.127(13)
_cell_length_b                   4.957(3)
_cell_length_c                   18.228(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.632(7)
_cell_angle_gamma                90
_cell_volume                     1884.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    908
_cell_measurement_theta_min      2.402
_cell_measurement_theta_max      22.973

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6273
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.611
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1903
_reflns_number_gt                918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1903
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.60587(8) 0.3596(3) 0.39726(11) 0.0781(6) Uani 1 1 d . . . . .
F2 F 0.58382(8) 0.6763(3) 0.45921(11) 0.0849(6) Uani 1 1 d . . . . .
F3 F 0.58715(8) 0.7531(3) 0.34630(11) 0.0806(6) Uani 1 1 d . . . . .
C1 C 0.67694(14) -0.1259(5) 0.69840(17) 0.0594(8) Uani 1 1 d . . . . .
H1 H 0.721471 -0.130536 0.720326 0.071 Uiso 1 1 calc R U . . .
C2 C 0.64490(16) -0.2920(5) 0.72897(18) 0.0668(9) Uani 1 1 d . . . . .
H2 H 0.667807 -0.409807 0.771374 0.080 Uiso 1 1 calc R U . . .
C3 C 0.57995(18) -0.2840(6) 0.6974(2) 0.0719(9) Uani 1 1 d . . . . .
H3 H 0.558560 -0.396325 0.718361 0.086 Uiso 1 1 calc R U . . .
C4 C 0.54578(16) -0.1127(7) 0.6350(2) 0.0807(10) Uani 1 1 d . . . . .
H4 H 0.501265 -0.108768 0.613554 0.097 Uiso 1 1 calc R U . . .
C5 C 0.57715(15) 0.0539(6) 0.60397(18) 0.0675(8) Uani 1 1 d . . . . .
H5 H 0.553839 0.171518 0.561702 0.081 Uiso 1 1 calc R U . . .
C6 C 0.64276(14) 0.0475(5) 0.63507(16) 0.0491(7) Uani 1 1 d . . . . .
C7 C 0.67443(14) 0.2206(5) 0.60133(17) 0.0551(7) Uani 1 1 d . . . . .
C8 C 0.69779(13) 0.3728(5) 0.57155(17) 0.0554(7) Uani 1 1 d . . . . .
C9 C 0.72364(14) 0.5622(5) 0.53474(16) 0.0485(7) Uani 1 1 d . . . . .
C10 C 0.68565(13) 0.6850(5) 0.46026(17) 0.0481(7) Uani 1 1 d . . . . .
C11 C 0.71215(14) 0.8688(5) 0.42680(16) 0.0508(7) Uani 1 1 d . . . . .
H11 H 0.686206 0.948462 0.377153 0.061 Uiso 1 1 calc R U . . .
C12 C 0.61650(14) 0.6197(6) 0.41652(19) 0.0588(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.331(3) . ?
F2 C12 1.328(3) . ?
F3 C12 1.336(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(3) . ?
C7 C8 1.187(3) . ?
C8 C9 1.427(3) . ?
C9 C11 1.383(4) 7_666 ?
C9 C10 1.398(4) . ?
C10 C11 1.379(3) . ?
C10 C12 1.481(4) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 121.3(3) . . ?
C8 C7 C6 176.4(3) . . ?
C7 C8 C9 177.7(3) . . ?
C11 C9 C10 118.1(2) 7_666 . ?
C11 C9 C8 120.0(2) 7_666 . ?
C10 C9 C8 121.9(3) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 C12 119.3(3) . . ?
C9 C10 C12 120.4(2) . . ?
C10 C11 C9 121.6(2) . 7_666 ?
C10 C11 H11 119.2 . . ?
C9 C11 H11 119.2 7_666 . ?
F2 C12 F1 105.8(2) . . ?
F2 C12 F3 106.0(2) . . ?
F1 C12 F3 105.5(2) . . ?
F2 C12 C10 113.2(2) . . ?
F1 C12 C10 112.7(2) . . ?
F3 C12 C10 113.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 179.4(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 -179.4(2) . . . . ?
C11 C9 C10 C11 0.1(4) 7_666 . . . ?
C8 C9 C10 C11 179.5(2) . . . . ?
C11 C9 C10 C12 -179.7(2) 7_666 . . . ?
C8 C9 C10 C12 -0.4(3) . . . . ?
C9 C10 C11 C9 -0.1(4) . . . 7_666 ?
C12 C10 C11 C9 179.7(2) . . . 7_666 ?
C11 C10 C12 F2 -120.0(3) . . . . ?
C9 C10 C12 F2 59.8(3) . . . . ?
C11 C10 C12 F1 119.9(2) . . . . ?
C9 C10 C12 F1 -60.3(3) . . . . ?
C11 C10 C12 F3 0.4(3) . . . . ?
C9 C10 C12 F3 -179.8(2) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2d
_database_code_depnum_ccdc_archive 'CCDC 2128027'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1094(18)
_cell_length_b                   13.026(2)
_cell_length_c                   7.5574(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.468(2)
_cell_angle_gamma                90
_cell_volume                     1084.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2107
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      23.582


_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6176
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1880
_reflns_number_gt                1541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.6886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1880
_refine_ls_number_parameters     180
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65192(17) 0.36249(16) 0.1949(3) 0.0561(6) Uani 1 1 d . . . . .
C1 C 0.9411(3) 0.3013(2) -0.3223(4) 0.0508(7) Uani 1 1 d . . . . .
H1 H 0.880570 0.251518 -0.331748 0.061 Uiso 1 1 calc R U . . .
C2 C 1.0494(3) 0.2809(3) -0.3846(4) 0.0546(8) Uani 1 1 d . . . . .
H2 H 1.061969 0.217412 -0.435367 0.065 Uiso 1 1 calc R U . . .
C3 C 1.1390(2) 0.3538(2) -0.3723(4) 0.0486(7) Uani 1 1 d . . . . .
C4 C 1.1197(3) 0.4480(3) -0.2982(4) 0.0575(8) Uani 1 1 d . . . . .
H4 H 1.180277 0.497690 -0.289778 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0121(3) 0.4685(2) -0.2372(4) 0.0551(8) Uani 1 1 d . . . . .
H5 H 0.999445 0.532727 -0.189148 0.066 Uiso 1 1 calc R U . . .
C6 C 0.9214(2) 0.3952(2) -0.2457(3) 0.0435(7) Uani 1 1 d . . . . .
C7 C 1.2564(3) 0.3326(3) -0.4386(5) 0.0680(10) Uani 1 1 d D . . . .
C8 C 0.8108(2) 0.4176(2) -0.1755(4) 0.0477(7) Uani 1 1 d . . . . .
C9 C 0.7207(2) 0.4389(2) -0.1148(4) 0.0455(7) Uani 1 1 d . . . . .
C10 C 0.6093(2) 0.4693(2) -0.0543(4) 0.0410(7) Uani 1 1 d . . . . .
C11 C 0.5736(2) 0.4295(2) 0.1026(4) 0.0414(7) Uani 1 1 d . . . . .
C12 C 0.4657(2) 0.4610(2) 0.1543(4) 0.0441(7) Uani 1 1 d . . . . .
H12 H 0.442180 0.434908 0.259067 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6199(3) 0.3235(3) 0.3576(5) 0.0720(11) Uani 1 1 d . . . . .
H13A H 0.545082 0.286060 0.334537 0.108 Uiso 1 1 calc R U . . .
H13B H 0.610122 0.379421 0.437221 0.108 Uiso 1 1 calc R U . . .
H13C H 0.682860 0.278603 0.411229 0.108 Uiso 1 1 calc R U . . .
F1 F 1.2850(10) 0.2365(8) -0.4367(15) 0.178(7) Uani 0.5 1 d D . P A 1
F2 F 1.3497(4) 0.3681(5) -0.3408(10) 0.086(2) Uani 0.5 1 d D . P A 1
F3 F 1.2549(11) 0.3574(10) -0.6000(12) 0.113(5) Uani 0.5 1 d D . P A 1
F2A F 1.3480(9) 0.3261(8) -0.3029(12) 0.050(3) Uiso 0.25 1 d D . P A 2
F3A F 1.2872(13) 0.4023(10) -0.538(2) 0.094(5) Uiso 0.25 1 d D . P A 2
F1A F 1.2658(12) 0.2516(10) -0.5192(19) 0.086(4) Uiso 0.25 1 d D . P A 2
F1B F 1.2437(18) 0.3583(13) -0.635(3) 0.071(5) Uiso 0.25 1 d . . P A 3
F2B F 1.2737(9) 0.2259(9) -0.4641(16) 0.040(2) Uiso 0.25 1 d . . P A 3
F3B F 1.3299(10) 0.4334(9) -0.4438(17) 0.090(3) Uiso 0.25 1 d . . P A 3


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.359(3) . ?
O1 C13 1.418(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 C7 1.483(4) . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C8 1.430(4) . ?
C7 F1A 1.230(11) . ?
C7 F3A 1.256(12) . ?
C7 F3 1.260(9) . ?
C7 F2 1.279(6) . ?
C7 F1 1.292(10) . ?
C7 F2A 1.351(10) . ?
C7 F2B 1.421(12) . ?
C7 F1B 1.508(19) . ?
C7 F3B 1.550(12) . ?
C8 C9 1.187(4) . ?
C9 C10 1.431(4) . ?
C10 C12 1.388(4) 3_665 ?
C10 C11 1.398(4) . ?
C11 C12 1.371(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C13 117.3(2) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 C7 120.7(3) . . ?
C4 C3 C7 119.6(3) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C8 121.8(3) . . ?
C5 C6 C8 119.8(3) . . ?
F1A C7 F3A 106.0(9) . . ?
F3 C7 F2 112.0(7) . . ?
F3 C7 F1 103.4(7) . . ?
F2 C7 F1 99.4(6) . . ?
F1A C7 F2A 102.6(8) . . ?
F3A C7 F2A 105.3(8) . . ?
F1A C7 C3 117.6(7) . . ?
F3A C7 C3 112.9(7) . . ?
F3 C7 C3 112.2(5) . . ?
F2 C7 C3 114.8(4) . . ?
F1 C7 C3 113.8(5) . . ?
F2A C7 C3 111.4(5) . . ?
F2B C7 C3 111.7(5) . . ?
F2B C7 F1B 94.6(8) . . ?
C3 C7 F1B 108.5(8) . . ?
F2B C7 F3B 138.1(6) . . ?
C3 C7 F3B 109.9(5) . . ?
F1B C7 F3B 76.7(8) . . ?
C9 C8 C6 177.9(3) . . ?
C8 C9 C10 175.3(3) . . ?
C12 C10 C11 119.2(2) 3_665 . ?
C12 C10 C9 119.4(2) 3_665 . ?
C11 C10 C9 121.4(3) . . ?
O1 C11 C12 124.8(2) . . ?
O1 C11 C10 116.1(2) . . ?
C12 C11 C10 119.0(2) . . ?
C11 C12 C10 121.7(3) . 3_665 ?
C11 C12 H12 119.1 . . ?
C10 C12 H12 119.1 3_665 . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C2 C3 C7 179.8(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C7 C3 C4 C5 179.9(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C6 C8 -178.4(3) . . . . ?
C4 C5 C6 C1 -1.8(5) . . . . ?
C4 C5 C6 C8 178.0(3) . . . . ?
C2 C3 C7 F1A 6.6(9) . . . . ?
C4 C3 C7 F1A -173.2(8) . . . . ?
C2 C3 C7 F3A 130.5(9) . . . . ?
C4 C3 C7 F3A -49.3(9) . . . . ?
C2 C3 C7 F3 90.1(8) . . . . ?
C4 C3 C7 F3 -89.7(8) . . . . ?
C2 C3 C7 F2 -140.5(5) . . . . ?
C4 C3 C7 F2 39.7(6) . . . . ?
C2 C3 C7 F1 -26.9(7) . . . . ?
C4 C3 C7 F1 153.4(7) . . . . ?
C2 C3 C7 F2A -111.3(6) . . . . ?
C4 C3 C7 F2A 68.9(6) . . . . ?
C2 C3 C7 F2B -16.4(7) . . . . ?
C4 C3 C7 F2B 163.8(6) . . . . ?
C2 C3 C7 F1B 86.6(8) . . . . ?
C4 C3 C7 F1B -93.2(8) . . . . ?
C2 C3 C7 F3B 168.7(6) . . . . ?
C4 C3 C7 F3B -11.1(7) . . . . ?
C13 O1 C11 C12 -0.9(4) . . . . ?
C13 O1 C11 C10 178.0(3) . . . . ?
C12 C10 C11 O1 -179.3(2) 3_665 . . . ?
C9 C10 C11 O1 1.3(4) . . . . ?
C12 C10 C11 C12 -0.4(4) 3_665 . . . ?
C9 C10 C11 C12 -179.8(3) . . . . ?
O1 C11 C12 C10 179.3(3) . . . 3_665 ?
C10 C11 C12 C10 0.4(5) . . . 3_665 ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.048


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e
_database_code_depnum_ccdc_archive 'CCDC 2128024'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   50.82(4)
_cell_length_b                   11.076(9)
_cell_length_c                   8.019(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.988(14)
_cell_angle_gamma                90
_cell_volume                     4508(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1330
_cell_measurement_theta_min      2.722
_cell_measurement_theta_max      19.835

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scnas'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12348
_diffrn_reflns_av_unetI/netI     0.1124
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4558
_reflns_number_gt                1828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4558
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1863
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.47232(5) 0.2805(2) 0.3382(4) 0.1083(10) Uani 1 1 d . . . . .
F2 F 0.46424(5) 0.2688(2) 0.5962(4) 0.1014(10) Uani 1 1 d . . . . .
F3 F 0.50220(5) 0.3245(2) 0.5241(5) 0.1252(13) Uani 1 1 d . . . . .
O1 O 0.31873(5) 0.1486(2) 0.1758(4) 0.0747(9) Uani 1 1 d . . . . .
C1 C 0.34494(7) 0.1370(3) 0.2205(5) 0.0525(10) Uani 1 1 d . . . . .
C2 C 0.35174(7) 0.0336(3) 0.3095(5) 0.0599(11) Uani 1 1 d . . . . .
H2 H 0.338771 -0.021270 0.336502 0.072 Uiso 1 1 calc R U . . .
C3 C 0.37749(7) 0.0120(3) 0.3578(5) 0.0596(11) Uani 1 1 d . . . . .
H3 H 0.381946 -0.057630 0.417604 0.071 Uiso 1 1 calc R U . . .
C4 C 0.39692(6) 0.0925(3) 0.3186(5) 0.0505(10) Uani 1 1 d . . . . .
C5 C 0.38973(7) 0.1961(3) 0.2317(5) 0.0600(11) Uani 1 1 d . . . . .
H5 H 0.402622 0.251715 0.205986 0.072 Uiso 1 1 calc R U . . .
C6 C 0.36379(7) 0.2185(3) 0.1823(5) 0.0559(11) Uani 1 1 d . . . . .
H6 H 0.359205 0.288486 0.123604 0.067 Uiso 1 1 calc R U . . .
C7 C 0.31026(8) 0.2512(5) 0.0839(6) 0.1057(19) Uani 1 1 d . . . . .
H7A H 0.318679 0.252800 -0.020445 0.158 Uiso 1 1 calc R U . . .
H7B H 0.314826 0.322728 0.146484 0.158 Uiso 1 1 calc R U . . .
H7C H 0.291497 0.247813 0.063196 0.158 Uiso 1 1 calc R U . . .
C8 C 0.42405(7) 0.0681(3) 0.3681(5) 0.0626(12) Uani 1 1 d . . . . .
C9 C 0.44647(8) 0.0498(4) 0.4088(5) 0.0678(12) Uani 1 1 d . . . . .
C10 C 0.47362(7) 0.0265(4) 0.4561(5) 0.0615(12) Uani 1 1 d . . . . .
C11 C 0.49162(7) 0.1194(4) 0.4915(5) 0.0625(12) Uani 1 1 d . . . . .
C12 C 0.51762(7) 0.0921(4) 0.5347(5) 0.0642(12) Uani 1 1 d . . . . .
H12 H 0.529496 0.154523 0.557970 0.077 Uiso 1 1 calc R U . . .
C13 C 0.48289(10) 0.2473(4) 0.4870(7) 0.0805(15) Uani 1 1 d . . . . .
F4 F 0.23494(6) 0.5061(3) 0.7491(4) 0.1347(14) Uani 1 1 d . . . . .
F5 F 0.27466(5) 0.5176(2) 0.7204(4) 0.1149(11) Uani 1 1 d . . . . .
F6 F 0.26071(9) 0.3971(3) 0.8908(4) 0.1596(17) Uani 1 1 d . . . . .
O2 O 0.42902(5) 0.3763(2) 0.8923(4) 0.0698(9) Uani 1 1 d . . . . .
C14 C 0.40310(7) 0.3750(3) 0.8367(5) 0.0488(10) Uani 1 1 d . . . . .
C15 C 0.38427(7) 0.4564(3) 0.8818(5) 0.0526(10) Uani 1 1 d . . . . .
H15 H 0.388803 0.519754 0.953698 0.063 Uiso 1 1 calc R U . . .
C16 C 0.35864(7) 0.4432(3) 0.8195(5) 0.0551(11) Uani 1 1 d . . . . .
H16 H 0.345874 0.497418 0.851725 0.066 Uiso 1 1 calc R U . . .
C17 C 0.35153(6) 0.3508(3) 0.7099(5) 0.0460(9) Uani 1 1 d . . . . .
C18 C 0.37099(7) 0.2715(3) 0.6630(5) 0.0541(10) Uani 1 1 d . . . . .
H18 H 0.366663 0.209230 0.588752 0.065 Uiso 1 1 calc R U . . .
C19 C 0.39649(7) 0.2839(3) 0.7250(5) 0.0582(11) Uani 1 1 d . . . . .
H19 H 0.409373 0.230677 0.691736 0.070 Uiso 1 1 calc R U . . .
C20 C 0.43723(8) 0.4674(4) 1.0068(7) 0.0920(17) Uani 1 1 d . . . . .
H20A H 0.433440 0.545237 0.958610 0.138 Uiso 1 1 calc R U . . .
H20B H 0.455837 0.460350 1.032177 0.138 Uiso 1 1 calc R U . . .
H20C H 0.427988 0.458624 1.107520 0.138 Uiso 1 1 calc R U . . .
C21 C 0.32462(7) 0.3338(3) 0.6513(5) 0.0528(10) Uani 1 1 d . . . . .
C22 C 0.30230(7) 0.3149(3) 0.6086(5) 0.0533(10) Uani 1 1 d . . . . .
C23 C 0.27557(7) 0.2856(3) 0.5563(4) 0.0452(9) Uani 1 1 d . . . . .
C24 C 0.25337(7) 0.3430(3) 0.6146(4) 0.0454(9) Uani 1 1 d . . . . .
C25 C 0.22857(6) 0.3078(3) 0.5583(4) 0.0486(10) Uani 1 1 d . . . . .
H25 H 0.214053 0.347664 0.598010 0.058 Uiso 1 1 calc R U . . .
C26 C 0.25585(9) 0.4393(4) 0.7435(6) 0.0708(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.335(5) . ?
F2 C13 1.345(5) . ?
F3 C13 1.324(5) . ?
O1 C1 1.367(4) . ?
O1 C7 1.409(5) . ?
C1 C6 1.363(5) . ?
C1 C2 1.383(5) . ?
C2 C3 1.366(4) . ?
C3 C4 1.379(5) . ?
C4 C5 1.382(5) . ?
C4 C8 1.440(5) . ?
C5 C6 1.379(4) . ?
C8 C9 1.186(4) . ?
C9 C10 1.435(5) . ?
C10 C12 1.388(5) 5_656 ?
C10 C11 1.396(5) . ?
C11 C12 1.382(4) . ?
C11 C13 1.484(6) . ?
F4 C26 1.298(5) . ?
F5 C26 1.311(5) . ?
F6 C26 1.283(5) . ?
O2 C14 1.369(4) . ?
O2 C20 1.413(4) . ?
C14 C15 1.377(5) . ?
C14 C19 1.380(5) . ?
C15 C16 1.378(4) . ?
C16 C17 1.385(5) . ?
C17 C18 1.389(5) . ?
C17 C21 1.435(5) . ?
C18 C19 1.371(4) . ?
C21 C22 1.186(4) . ?
C22 C23 1.438(5) . ?
C23 C25 1.392(5) 7_556 ?
C23 C24 1.397(5) . ?
C24 C25 1.373(4) . ?
C24 C26 1.486(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 118.7(3) . . ?
C6 C1 O1 124.4(3) . . ?
C6 C1 C2 120.3(3) . . ?
O1 C1 C2 115.3(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 120.6(3) . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 C8 120.2(3) . . ?
C5 C4 C8 121.3(4) . . ?
C6 C5 C4 121.2(3) . . ?
C1 C6 C5 119.2(3) . . ?
C9 C8 C4 179.0(4) . . ?
C8 C9 C10 179.2(5) . . ?
C12 C10 C11 118.8(3) 5_656 . ?
C12 C10 C9 119.1(4) 5_656 . ?
C11 C10 C9 122.1(4) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 C13 119.7(4) . . ?
C10 C11 C13 120.4(3) . . ?
C11 C12 C10 121.3(4) . 5_656 ?
F3 C13 F1 106.4(4) . . ?
F3 C13 F2 106.2(4) . . ?
F1 C13 F2 105.6(4) . . ?
F3 C13 C11 113.2(4) . . ?
F1 C13 C11 113.0(4) . . ?
F2 C13 C11 111.9(4) . . ?
C14 O2 C20 117.7(3) . . ?
O2 C14 C15 125.3(3) . . ?
O2 C14 C19 114.6(3) . . ?
C15 C14 C19 120.0(3) . . ?
C14 C15 C16 119.5(3) . . ?
C15 C16 C17 121.2(3) . . ?
C16 C17 C18 118.3(3) . . ?
C16 C17 C21 121.1(3) . . ?
C18 C17 C21 120.5(3) . . ?
C19 C18 C17 120.8(3) . . ?
C18 C19 C14 120.2(3) . . ?
C22 C21 C17 176.6(4) . . ?
C21 C22 C23 177.1(4) . . ?
C25 C23 C24 117.5(3) 7_556 . ?
C25 C23 C22 117.9(3) 7_556 . ?
C24 C23 C22 124.5(3) . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 C26 118.4(4) . . ?
C23 C24 C26 121.3(3) . . ?
C24 C25 C23 122.2(3) . 7_556 ?
F6 C26 F4 107.1(5) . . ?
F6 C26 F5 105.3(4) . . ?
F4 C26 F5 103.4(4) . . ?
F6 C26 C24 112.6(4) . . ?
F4 C26 C24 113.2(3) . . ?
F5 C26 C24 114.4(4) . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.050


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2a
_database_code_depnum_ccdc_archive 'CCDC 2128025'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 O2'
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.569(5)
_cell_length_b                   11.084(3)
_cell_length_c                   10.773(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.868(4)
_cell_angle_gamma                90
_cell_volume                     1819.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1988
_cell_measurement_theta_min      2.272
_cell_measurement_theta_max      24.394

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS


_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6625
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.799
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1854
_reflns_number_gt                1360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'SAINT+ v. 8.37 (Bruker AXS)'
_computing_data_reduction        'SAINT+ v. 8.37 (Bruker AXS)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53402(10) 0.76373(10) -0.05088(13) 0.0688(4) Uani 1 1 d . . . . .
C1 C 0.40056(12) 0.57226(15) 0.31358(16) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.456201 0.602287 0.347558 0.060 Uiso 1 1 calc R U . . .
C2 C 0.36929(13) 0.47424(16) 0.36904(17) 0.0593(5) Uani 1 1 d . . . . .
H2 H 0.404062 0.437708 0.439543 0.071 Uiso 1 1 calc R U . . .
C3 C 0.28704(13) 0.43053(16) 0.32043(18) 0.0587(5) Uani 1 1 d . . . . .
H3 H 0.265887 0.364384 0.358018 0.070 Uiso 1 1 calc R U . . .
C4 C 0.23598(12) 0.48406(17) 0.21668(18) 0.0582(5) Uani 1 1 d . . . . .
H4 H 0.179969 0.454444 0.184281 0.070 Uiso 1 1 calc R U . . .
C5 C 0.26690(11) 0.58159(16) 0.15976(16) 0.0512(5) Uani 1 1 d . . . . .
H5 H 0.231826 0.617223 0.088943 0.061 Uiso 1 1 calc R U . . .
C6 C 0.34983(10) 0.62662(13) 0.20751(14) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.38514(10) 0.72608(13) 0.14847(14) 0.0406(4) Uani 1 1 d . . . . .
C8 C 0.41907(10) 0.80649(14) 0.10295(14) 0.0407(4) Uani 1 1 d . . . . .
C9 C 0.46002(10) 0.90395(13) 0.05012(14) 0.0383(4) Uani 1 1 d . . . . .
C10 C 0.51945(10) 0.88192(13) -0.02774(15) 0.0428(4) Uani 1 1 d . . . . .
C11 C 0.44138(11) 1.02257(14) 0.07699(15) 0.0432(4) Uani 1 1 d . . . . .
H11 H 0.401838 1.037902 0.129068 0.052 Uiso 1 1 calc R U . . .
C12 C 0.60279(19) 0.73562(19) -0.1149(3) 0.0936(9) Uani 1 1 d . . . . .
H12A H 0.589523 0.769349 -0.198762 0.140 Uiso 1 1 calc R U . . .
H12B H 0.608322 0.649629 -0.120406 0.140 Uiso 1 1 calc R U . . .
H12C H 0.656942 0.768929 -0.068803 0.140 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.3613(19) . ?
O1 C12 1.422(2) . ?
C1 C2 1.376(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.369(3) . ?
C3 C4 1.367(3) . ?
C4 C5 1.378(2) . ?
C5 C6 1.381(2) . ?
C6 C7 1.437(2) . ?
C7 C8 1.192(2) . ?
C8 C9 1.431(2) . ?
C9 C11 1.390(2) . ?
C9 C10 1.392(2) . ?
C10 C11 1.381(2) 5_675 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C12 118.03(15) . . ?
C2 C1 C6 120.57(16) . . ?
C3 C2 C1 120.00(17) . . ?
C4 C3 C2 120.02(16) . . ?
C3 C4 C5 120.46(17) . . ?
C4 C5 C6 120.21(16) . . ?
C5 C6 C1 118.72(14) . . ?
C5 C6 C7 121.71(15) . . ?
C1 C6 C7 119.56(14) . . ?
C8 C7 C6 176.27(17) . . ?
C7 C8 C9 179.13(17) . . ?
C11 C9 C10 118.98(13) . . ?
C11 C9 C8 120.15(14) . . ?
C10 C9 C8 120.86(14) . . ?
O1 C10 C11 124.33(15) . 5_675 ?
O1 C10 C9 115.82(13) . . ?
C11 C10 C9 119.84(14) 5_675 . ?
C10 C11 C9 121.18(14) 5_675 . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c
_database_code_depnum_ccdc_archive 'CCDC 2128023'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.656(6)
_cell_length_b                   11.264(8)
_cell_length_c                   11.003(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.45(3)
_cell_angle_gamma                90
_cell_volume                     1066.1(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    354
_cell_measurement_theta_min      2.596
_cell_measurement_theta_max      17.532

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5990
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1863
_reflns_number_gt                866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'SAINT+ v. 8.37 (Bruker AXS)'
_computing_data_reduction        'SAINT+ v. 8.37 (Bruker AXS)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1214P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.083(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1631
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.2515
_refine_ls_wR_factor_gt          0.1923
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7565(4) 0.4013(4) 0.2343(3) 0.1055(14) Uani 1 1 d . . . . .
F2 F 0.8208(4) 0.5766(3) 0.1971(3) 0.0931(13) Uani 1 1 d . . . . .
F3 F 0.9786(4) 0.4376(3) 0.1777(3) 0.0948(13) Uani 1 1 d . . . . .
O1 O 0.4076(4) 0.6160(3) 0.1762(3) 0.0718(12) Uani 1 1 d . . . . .
C1 C 0.3311(5) 0.6674(4) 0.2640(5) 0.0527(13) Uani 1 1 d . . . . .
C2 C 0.1868(5) 0.7187(5) 0.2442(5) 0.0654(16) Uani 1 1 d . . . . .
H2 H 0.133947 0.719996 0.165788 0.078 Uiso 1 1 calc R U . . .
C3 C 0.1205(6) 0.7678(5) 0.3390(6) 0.0733(17) Uani 1 1 d . . . . .
H3 H 0.023133 0.803180 0.324091 0.088 Uiso 1 1 calc R U . . .
C4 C 0.1944(6) 0.7663(5) 0.4560(5) 0.0667(16) Uani 1 1 d . . . . .
H4 H 0.147595 0.799247 0.520203 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3383(5) 0.7154(4) 0.4764(5) 0.0587(15) Uani 1 1 d . . . . .
H5 H 0.388992 0.713592 0.555535 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4098(5) 0.6666(4) 0.3825(5) 0.0489(13) Uani 1 1 d . . . . .
C7 C 0.3239(6) 0.6026(5) 0.0569(5) 0.0764(18) Uani 1 1 d . . . . .
H7A H 0.230967 0.557510 0.062916 0.115 Uiso 1 1 calc R U . . .
H7B H 0.387940 0.561753 0.004533 0.115 Uiso 1 1 calc R U . . .
H7C H 0.296897 0.679439 0.023316 0.115 Uiso 1 1 calc R U . . .
C8 C 0.5630(5) 0.6162(4) 0.4064(5) 0.0540(13) Uani 1 1 d . . . . .
C9 C 0.6926(5) 0.5806(4) 0.4293(4) 0.0530(14) Uani 1 1 d . . . . .
C10 C 0.8480(5) 0.5392(4) 0.4628(4) 0.0473(13) Uani 1 1 d . . . . .
C11 C 0.9390(5) 0.4899(4) 0.3805(4) 0.0507(13) Uani 1 1 d . . . . .
C12 C 0.9116(5) 0.5483(4) 0.5846(5) 0.0507(13) Uani 1 1 d . . . . .
H12 H 0.852978 0.580330 0.642393 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8747(6) 0.4766(6) 0.2486(5) 0.0652(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.325(6) . ?
F2 C13 1.322(6) . ?
F3 C13 1.329(6) . ?
O1 C1 1.361(6) . ?
O1 C7 1.434(6) . ?
C1 C2 1.371(6) . ?
C1 C6 1.402(6) . ?
C2 C3 1.363(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9300 . ?
C6 C8 1.439(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.191(6) . ?
C9 C10 1.432(6) . ?
C10 C11 1.382(6) . ?
C10 C12 1.394(7) . ?
C11 C12 1.376(6) 3_766 ?
C11 C13 1.503(7) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.3(4) . . ?
O1 C1 C2 125.0(5) . . ?
O1 C1 C6 115.6(4) . . ?
C2 C1 C6 119.3(5) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.7(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 C8 120.2(4) . . ?
C1 C6 C8 120.9(5) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C6 176.1(5) . . ?
C8 C9 C10 177.3(5) . . ?
C11 C10 C12 117.8(4) . . ?
C11 C10 C9 123.3(4) . . ?
C12 C10 C9 118.8(4) . . ?
C12 C11 C10 122.0(4) 3_766 . ?
C12 C11 C13 118.2(5) 3_766 . ?
C10 C11 C13 119.8(4) . . ?
C11 C12 C10 120.2(4) 3_766 . ?
C11 C12 H12 119.9 3_766 . ?
C10 C12 H12 119.9 . . ?
F2 C13 F1 105.3(4) . . ?
F2 C13 F3 105.0(5) . . ?
F1 C13 F3 106.5(5) . . ?
F2 C13 C11 113.8(5) . . ?
F1 C13 C11 112.1(5) . . ?
F3 C13 C11 113.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C2 -7.4(7) . . . . ?
C7 O1 C1 C6 172.9(4) . . . . ?
O1 C1 C2 C3 180.0(5) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 -0.8(9) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 C1 -1.3(7) . . . . ?
C4 C5 C6 C8 178.5(5) . . . . ?
O1 C1 C6 C5 -178.9(4) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
O1 C1 C6 C8 1.2(7) . . . . ?
C2 C1 C6 C8 -178.5(5) . . . . ?
C12 C10 C11 C12 -0.7(8) . . . 3_766 ?
C9 C10 C11 C12 179.6(5) . . . 3_766 ?
C12 C10 C11 C13 179.1(5) . . . . ?
C9 C10 C11 C13 -0.6(8) . . . . ?
C11 C10 C12 C11 0.7(8) . . . 3_766 ?
C9 C10 C12 C11 -179.6(4) . . . 3_766 ?
C12 C11 C13 F2 -125.8(5) 3_766 . . . ?
C10 C11 C13 F2 54.4(7) . . . . ?
C12 C11 C13 F1 114.9(5) 3_766 . . . ?
C10 C11 C13 F1 -64.9(7) . . . . ?
C12 C11 C13 F3 -5.7(7) 3_766 . . . ?
C10 C11 C13 F3 174.5(5) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.096


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2b
_database_code_depnum_ccdc_archive 'CCDC 2128026'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.880(19)
_cell_length_b                   10.813(8)
_cell_length_c                   8.582(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.551(8)
_cell_angle_gamma                90
_cell_volume                     2178(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2003
_cell_measurement_theta_min      3.213
_cell_measurement_theta_max      23.550

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS


_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6198
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.414
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1904
_reflns_number_gt                1529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'SAINT+ v. 8.37 (Bruker AXS)'
_computing_data_reduction        'SAINT+ v. 8.37 (Bruker AXS)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2016)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+4.3144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2457
_refine_ls_wR_factor_gt          0.2323
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61057(13) 0.0489(3) 0.4749(4) 0.0632(10) Uani 1 1 d . . . . .
C1 C 0.65728(19) 0.4622(4) 0.7152(6) 0.0500(11) Uani 1 1 d . . . . .
C2 C 0.6765(3) 0.5806(5) 0.7578(7) 0.0732(17) Uani 1 1 d . . . . .
H2 H 0.715236 0.594670 0.790897 0.088 Uiso 1 1 calc R U . . .
C3 C 0.6397(3) 0.6752(5) 0.7517(8) 0.086(2) Uani 1 1 d . . . . .
H3 H 0.653612 0.754062 0.779364 0.103 Uiso 1 1 calc R U . . .
C4 C 0.5832(3) 0.6582(5) 0.7064(7) 0.0752(17) Uani 1 1 d . . . . .
H4 H 0.558119 0.724359 0.703880 0.090 Uiso 1 1 calc R U . . .
C5 C 0.5632(2) 0.5422(5) 0.6642(6) 0.0620(14) Uani 1 1 d . . . . .
H5 H 0.524236 0.530496 0.632111 0.074 Uiso 1 1 calc R U . . .
C6 C 0.59937(18) 0.4413(4) 0.6678(5) 0.0438(10) Uani 1 1 d . . . . .
C7 C 0.6983(2) 0.3604(6) 0.7312(8) 0.0674(15) Uani 1 1 d . . . . .
C8 C 0.57471(17) 0.3238(4) 0.6237(5) 0.0456(11) Uani 1 1 d . . . . .
C9 C 0.55106(17) 0.2310(4) 0.5854(5) 0.0463(11) Uani 1 1 d . . . . .
C10 C 0.52538(17) 0.1138(4) 0.5398(5) 0.0426(10) Uani 1 1 d . . . . .
C11 C 0.55611(16) 0.0194(4) 0.4850(5) 0.0426(10) Uani 1 1 d . . . . .
C12 C 0.53116(17) -0.0923(4) 0.4463(5) 0.0450(11) Uani 1 1 d . . . . .
H12 H 0.552061 -0.155224 0.410180 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6441(2) -0.0421(5) 0.4242(8) 0.0701(16) Uani 1 1 d . . . . .
H13A H 0.627429 -0.067392 0.318642 0.105 Uiso 1 1 calc R U . . .
H13B H 0.646528 -0.111991 0.494152 0.105 Uiso 1 1 calc R U . . .
H13C H 0.681634 -0.009988 0.424689 0.105 Uiso 1 1 calc R U . . .
F1 F 0.75017(16) 0.3955(5) 0.7435(10) 0.180(3) Uani 1 1 d . . . A 1
F2 F 0.6985(3) 0.2952(5) 0.8546(7) 0.157(2) Uani 1 1 d . . . B 1
F3 F 0.69015(19) 0.2788(5) 0.6226(7) 0.139(2) Uani 1 1 d . . . C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.357(5) . ?
O1 C13 1.389(6) . ?
C1 C2 1.386(7) . ?
C1 C6 1.387(6) . ?
C1 C7 1.463(7) . ?
C2 C3 1.342(8) . ?
C3 C4 1.348(9) . ?
C4 C5 1.367(7) . ?
C5 C6 1.388(7) . ?
C6 C8 1.422(6) . ?
C7 F2 1.272(7) . ?
C7 F3 1.273(7) . ?
C7 F1 1.280(6) . ?
C8 C9 1.168(6) . ?
C9 C10 1.431(6) . ?
C10 C11 1.388(6) . ?
C10 C12 1.397(6) 5_656 ?
C11 C12 1.361(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C13 117.9(4) . . ?
C2 C1 C6 119.4(5) . . ?
C2 C1 C7 119.1(5) . . ?
C6 C1 C7 121.3(4) . . ?
C3 C2 C1 120.8(5) . . ?
C2 C3 C4 121.4(5) . . ?
C3 C4 C5 118.9(6) . . ?
C4 C5 C6 122.0(5) . . ?
C1 C6 C5 117.5(4) . . ?
C1 C6 C8 124.4(4) . . ?
C5 C6 C8 118.1(4) . . ?
F2 C7 F3 101.6(6) . . ?
F2 C7 F1 103.9(6) . . ?
F3 C7 F1 106.4(6) . . ?
F2 C7 C1 113.3(5) . . ?
F3 C7 C1 116.3(5) . . ?
F1 C7 C1 114.0(5) . . ?
C9 C8 C6 175.6(5) . . ?
C8 C9 C10 176.5(5) . . ?
C11 C10 C12 119.1(4) . 5_656 ?
C11 C10 C9 121.1(4) . . ?
C12 C10 C9 119.8(4) 5_656 . ?
O1 C11 C12 125.1(4) . . ?
O1 C11 C10 114.9(4) . . ?
C12 C11 C10 120.0(4) . . ?
C11 C12 C10 120.9(4) . 5_656 ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2e
_database_code_depnum_ccdc_archive 'CCDC 2128028'
loop_
_audit_author_name
_audit_author_address
'Ana Maria Rodriguez'
;Universidad de Castilla la Mancha
Spain
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.14(8)
_cell_length_b                   8.41(9)
_cell_length_c                   9.10(9)
_cell_angle_alpha                64.74(9)
_cell_angle_beta                 89.93(11)
_cell_angle_gamma                66.50(10)
_cell_volume                     506(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    140
_cell_measurement_theta_min      2.876
_cell_measurement_theta_max      16.382

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS


_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEX2'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2921
_diffrn_reflns_av_unetI/netI     0.6726
_diffrn_reflns_av_R_equivalents  0.3633
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             1705
_reflns_number_gt                242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v. 2016.1.0 (Bruker AXS, 2016)'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2012)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1705
_refine_ls_number_parameters     158
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.3822
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1560
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   0.653
_refine_ls_restrained_S_all      0.636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.8125(8) 0.5013(9) 0.3845(7) 0.094(3) Uani 1 1 d . . . . .
C1 C 0.5960(14) 0.5289(14) 0.7276(11) 0.086(5) Uani 1 1 d . . . . .
H1 H 0.607831 0.453554 0.840633 0.104 Uiso 1 1 calc R U . . .
C2 C 0.7179(13) 0.4451(13) 0.6488(11) 0.077(4) Uani 1 1 d . . . . .
H2 H 0.804413 0.314878 0.704116 0.093 Uiso 1 1 calc R U . . .
C3 C 0.7071(13) 0.5599(14) 0.4867(12) 0.067(4) Uani 1 1 d . . . . .
C4 C 0.5694(13) 0.7487(14) 0.4007(11) 0.078(4) Uani 1 1 d . . . . .
H4 H 0.556974 0.822521 0.287301 0.094 Uiso 1 1 calc R U . . .
C5 C 0.4498(13) 0.8252(13) 0.4888(11) 0.077(4) Uani 1 1 d . . . . .
H5 H 0.361534 0.954746 0.434756 0.093 Uiso 1 1 calc R U . . .
C6 C 0.4602(12) 0.7125(14) 0.6539(11) 0.056(3) Uani 1 1 d . . . . .
C7 C 0.9563(12) 0.3059(13) 0.4657(11) 0.090(5) Uani 1 1 d . . . . .
H7A H 1.035717 0.284931 0.391052 0.134 Uiso 1 1 calc R U . . .
H7B H 0.904429 0.214451 0.498565 0.134 Uiso 1 1 calc R U . . .
H7C H 1.025047 0.287338 0.562114 0.134 Uiso 1 1 calc R U . . .
C8 C 0.3339(12) 0.7888(12) 0.7420(10) 0.054(3) Uani 1 1 d . . . . .
C9 C 0.2355(13) 0.8511(13) 0.8170(11) 0.067(4) Uani 1 1 d . . . . .
C10 C 0.1136(14) 0.9292(14) 0.9089(11) 0.057(3) Uani 1 1 d . . . . .
C11 C -0.0290(16) 0.8800(15) 0.9410(13) 0.069(3) Uani 1 1 d . . . . .
C12 C 0.1548(16) 1.0431(15) 0.9643(11) 0.062(3) Uani 1 1 d . . . . .
O2 O -0.0618(15) 0.7668(15) 0.8915(12) 0.076(3) Uani 0.7 1 d . . P A 1
C13 C -0.208(2) 0.713(3) 0.936(2) 0.090(6) Uani 0.7 1 d . . P A 1
H13A H -0.323494 0.825492 0.877783 0.135 Uiso 0.7 1 calc R U P A 1
H13B H -0.201840 0.665344 1.053664 0.135 Uiso 0.7 1 calc R U P A 1
H13C H -0.197321 0.612453 0.907639 0.135 Uiso 0.7 1 calc R U P A 1
O2A O 0.295(3) 1.091(3) 0.953(2) 0.063(6) Uani 0.3 1 d . U P B 2
C13A C 0.322(6) 1.208(7) 1.017(6) 0.117(16) Uani 0.3 1 d . . P B 2
H13D H 0.360594 1.297829 0.937162 0.175 Uiso 0.3 1 calc R U P B 2
H13E H 0.413637 1.125112 1.117456 0.175 Uiso 0.3 1 calc R U P B 2
H13F H 0.208805 1.279982 1.040545 0.175 Uiso 0.3 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C3 1.377(12) . ?
O3 C7 1.431(14) . ?
C1 C6 1.346(14) . ?
C1 C2 1.366(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.355(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(14) . ?
C4 C5 1.393(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(16) . ?
C5 H5 0.9300 . ?
C6 C8 1.422(13) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.163(11) . ?
C9 C10 1.436(13) . ?
C10 C11 1.371(19) . ?
C10 C12 1.398(18) . ?
C11 O2 1.323(18) . ?
C11 C12 1.468(14) 2_577 ?
C12 O2A 1.35(3) . ?
O2 C13 1.44(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O2A C13A 1.42(4) . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O3 C7 114.9(9) . . ?
C6 C1 C2 124.9(10) . . ?
C6 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C3 C2 C1 117.1(10) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 O3 126.0(10) . . ?
C2 C3 C4 121.5(8) . . ?
O3 C3 C4 112.1(10) . . ?
C3 C4 C5 118.2(10) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.1(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 116.9(8) . . ?
C1 C6 C8 122.1(10) . . ?
C5 C6 C8 121.0(10) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C6 177.6(12) . . ?
C8 C9 C10 179.7(12) . . ?
C11 C10 C12 125.3(10) . . ?
C11 C10 C9 117.7(13) . . ?
C12 C10 C9 117.0(12) . . ?
O2 C11 C10 124.2(11) . . ?
O2 C11 C12 117.1(14) . 2_577 ?
C10 C11 C12 118.7(13) . 2_577 ?
O2A C12 C10 131.7(13) . . ?
C10 C12 C11 115.9(13) . 2_577 ?
C11 O2 C13 121.3(12) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 O2A C13A 126(2) . . ?
O2A C13A H13D 109.5 . . ?
O2A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
O2A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 4.1(18) . . . . ?
C1 C2 C3 O3 -177.5(11) . . . . ?
C1 C2 C3 C4 -5.3(17) . . . . ?
C7 O3 C3 C2 -6.4(16) . . . . ?
C7 O3 C3 C4 -179.2(11) . . . . ?
C2 C3 C4 C5 5.5(18) . . . . ?
O3 C3 C4 C5 178.7(10) . . . . ?
C3 C4 C5 C6 -4.3(18) . . . . ?
C2 C1 C6 C5 -3.0(19) . . . . ?
C2 C1 C6 C8 177.8(11) . . . . ?
C4 C5 C6 C1 3.0(17) . . . . ?
C4 C5 C6 C8 -177.7(11) . . . . ?
C12 C10 C11 O2 -177.8(11) . . . . ?
C9 C10 C11 O2 -0.6(17) . . . . ?
C12 C10 C11 C12 2.4(18) . . . 2_577 ?
C9 C10 C11 C12 179.6(8) . . . 2_577 ?
C11 C10 C12 O2A 174.8(16) . . . . ?
C9 C10 C12 O2A -2(2) . . . . ?
C11 C10 C12 C11 -2.3(18) . . . 2_577 ?
C9 C10 C12 C11 -179.5(8) . . . 2_577 ?
C10 C11 O2 C13 176.9(14) . . . . ?
C12 C11 O2 C13 -3.3(18) 2_577 . . . ?
C10 C12 O2A C13A -179(3) . . . . ?
C11 C12 O2A C13A -2(4) 2_577 . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053




# start Validation Reply Form
_vrf_RINTA01_2e                  
;
PROBLEM:
The value of Rint is greater than 0.25    Rint given   0.363
RESPONSE:
For this alert and related: The crystal has diffracted weakly 
and better data than those presented could not be obtained.
We think this resolution is sufficient for the purpose of publication work.
;
# end Validation Reply Form
